Modification of anionic cyanine dyes and application in cysteine detection

IF 4.1 3区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Photochemistry and Photobiology A-chemistry Pub Date : 2025-01-29 DOI:10.1016/j.jphotochem.2024.116250

Chen Luo , Huijin Lin , Huihui Cai , Chaobiao Huang

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Abstract

Anionic cyanine is an organic fluorescent dye with excellent optical properties. Compared to cationic cyanine, anionic cyanine has been less studied and applied due to the lack of modification sites. However, when the cyclohexene ring in the anionic cyanine skeleton is replaced by a tetrahydropyridine ring, the modification site will be added, forming a novel cyanine dye AHC-N-R with NIR emission. Photophysical properties show that this anionic cyanine retains the excellent optical properties of conventional cyanine and is expected to adjust the fluorescence emission by changing the substituent groups. Acrylates were introduced in this dye to synthesize the cysteine fluorescent probe AHC-NBn-AE. The amino and sulfhydryl groups in cysteine condense with acrylate to form 1,4-thiazepane analogs and release fluorophores AHC-NBn-OH, restoring fluorescence at 650 nm. The fluorescence recovery of the probe was linearly related to the concentration of cysteine for 0.3–50.0 μmol/L. The detection limit was 0.1 μmol/L (S/N = 3, n = 9). There was almost no interference with DL-homocysteine, glutathione and several common amino acids to cysteine. The cysteine content of the L-cysteine capsule was successfully tested. The recovery rate was 94.4 %–101.5 %.

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来源期刊

Journal of Photochemistry and Photobiology A-chemistry 化学-物理化学

CiteScore

7.90

自引率

7.00%

发文量

580

审稿时长

48 days

期刊介绍： JPPA publishes the results of fundamental studies on all aspects of chemical phenomena induced by interactions between light and molecules/matter of all kinds. All systems capable of being described at the molecular or integrated multimolecular level are appropriate for the journal. This includes all molecular chemical species as well as biomolecular, supramolecular, polymer and other macromolecular systems, as well as solid state photochemistry. In addition, the journal publishes studies of semiconductor and other photoactive organic and inorganic materials, photocatalysis (organic, inorganic, supramolecular and superconductor). The scope includes condensed and gas phase photochemistry, as well as synchrotron radiation chemistry. A broad range of processes and techniques in photochemistry are covered such as light induced energy, electron and proton transfer; nonlinear photochemical behavior; mechanistic investigation of photochemical reactions and identification of the products of photochemical reactions; quantum yield determinations and measurements of rate constants for primary and secondary photochemical processes; steady-state and time-resolved emission, ultrafast spectroscopic methods, single molecule spectroscopy, time resolved X-ray diffraction, luminescence microscopy, and scattering spectroscopy applied to photochemistry. Papers in emerging and applied areas such as luminescent sensors, electroluminescence, solar energy conversion, atmospheric photochemistry, environmental remediation, and related photocatalytic chemistry are also welcome.